Catalysis with Supramolecular Carbon-Bonding Interactions

Angew Chem Int Ed Engl. 2021 Oct 11;60(42):22717-22721. doi: 10.1002/anie.202108973. Epub 2021 Sep 13.

Abstract

Herein, we describe a new catalysis platform, supramolecular carbon-bonding catalysis, which exploits the highly directional weak interactions between carbon centers of catalysts and electron donors to drive chemical reactions. To demonstrate this catalysis approach, we discovered a class of cyclopropane derivatives incorporated with carbonyl, ester and cyano groups as catalysts which showed general catalysis capability in different types of benchmark reactions. Among these typical examples, a challenging tail-to-head terpene cyclization can be achieved by supramolecular carbon-bonding catalysis. The co-crystal structures of catalyst and electron donors, comparison experiments, and titrations support a catalysis mode of carbon-bonding activation of Lewis basic reactants.

Keywords: carbon-bonding; catalysts; noncovalent interactions; supramolecular catalysis; terpene cyclization.